Reaction of red phosphorus with allylbenzene in superbasic system KOH-DMSO

Article abstract of DOI:10.1080/10426507.2010.528478

Red phosphorus reacts with allylbenzene in the superbase system KOH-DMSO (130C, 3 h, Ar) to give a mixture of bis(1-methyl-2-phenylethyl)phosphane (1), bis(1-methyl-2-phenylethyl)phosphane oxide (2), and 1-methyl-2- phenylethylphosphinic acid (3). Secondary phosphane oxide 2 and phosphinic acid 3 have been isolated from this mixture in 35% and 32% yield, respectively. Microwave activation of the reaction (200 W, 30 min) affords secondary phosphane 1 as the main product in 48% yield. Copyright Taylor &Francis Group, LLC.

Full text of DOI:10.1080/10426507.2010.528478

This article was downloaded by: [Aston University]
On: 13 January 2014, At: 17:36
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Phosphorus, Sulfur, and Silicon and the
Related Elements
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/gpss20
Reaction of Red Phosphorus with
Allylbenzene in Superbasic System KOH-
DMSO
Svetlana F. Malysheva a , Natal’ya A. Belogorlova a , Nina K.
Gusarova a , Alexander V. Artem’ev a , Alexander I. Albanov a & Boris
A. Trofimov a
a A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the
Russian Academy of Sciences , Irkutsk, Russia
Published online: 11 Aug 2011.
To cite this article: Svetlana F. Malysheva , Natal’ya A. Belogorlova , Nina K. Gusarova , Alexander
V. Artem’ev , Alexander I. Albanov & Boris A. Trofimov (2011) Reaction of Red Phosphorus with
Allylbenzene in Superbasic System KOH-DMSO, Phosphorus, Sulfur, and Silicon and the Related
Elements, 186:8, 1688-1693, DOI: 10.1080/10426507.2010.528478
To link to this article: http://dx.doi.org/10.1080/10426507.2010.528478
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or
howsoever caused arising directly or indirectly in connection with, in relation to or arising
out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden. Terms &

Conditions of access and use can be found at http://www.tandfonline.com/page/terms-
and-conditions

Phosphorus, Sulfur, and Silicon, 186:1688–1693, 2011
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2010.528478
REACTION OF RED PHOSPHORUS WITH ALLYLBENZENE
IN SUPERBASIC SYSTEM KOH-DMSO
Svetlana F. Malysheva, Natal’ya A. Belogorlova,
Nina K. Gusarova, Alexander V. Artem’ev,
Alexander I. Albanov, and Boris A. Trofimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian
Academy of Sciences, Irkutsk, Russia
GRAPHICAL ABSTRACT
Abstract Red phosphorus reacts with allylbenzene in the superbase system KOH-DMSO
(130◦C, 3 h, Ar) to give a mixture of bis(1-methyl-2-phenylethyl)phosphane (1), bis(1-methyl-
2-phenylethyl)phosphane oxide (2), and 1-methyl-2-phenylethylphosphinic acid (3). Secondary
phosphane oxide 2 and phosphinic acid 3 have been isolated from this mixture in 35% and 32%
yield, respectively. Microwave activation of the reaction (200 W, 30 min) affords secondary
phosphane 1 as the main product in 48% yield.
Keywords Allylbenzene; microwave irradiation; phosphinic acid; red phosphorus; secondary
phosphane; secondary phosphane oxide; superbase system
INTRODUCTION
In recent years, the cleavage of the P–P bond of elemental phosphorus under the action
of nucleophiles has been studied.1 Fundamentally, these investigations essentially supple-
ment the existing paradigms in phosphorus chemistry. From the viewpoint of synthetic
Received 6 July 2010; accepted 27 September 2010.
Financial support from the Russian Foundation for Basic Research (grant no. 08-03-00251) is gratefully
acknowledged.
Address correspondence to Boris A. Trofimov, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian
Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia. E-mail: boris trofimov@
irioch.irk.ru
1688

REACTION OF RED PHOSPHORUS WITH ALLYLBENZENE
1689
methodology, they open the shortest and environmentally benign ways to the practically
important organophosphorus compounds.1 The possibility of preparative use of phosphorus-
centered nucleophiles produced by the cleavage of P–P bonds of white phosphorus under
the action of hydroxide anions was reported for the first time in 1963.2 Successful attempts
to utilize the less reactive but nontoxic red phosphorus in organophosphorus synthesis were
made by Bogolyubov and Petrov3 and Bornancini et al.4 who accomplished the cleavage
of P–P bond of three-dimensional macromolecule of red phosphorus in alkali metal–liquid
ammonia systems. A direct synthesis of tristyrylphosphane5 from phenylacetylene and red
phosphorus in the KOH-HMPA superbasic system laid the foundation of the systematic
application of phosphorus-centered nucleophiles for the preparation of unavailable or un-
known organophosphorus compounds. For example, a facile one-pot synthesis of tertiary
phosphane oxides by nucleophilic addition of phosphinite anions to vinylarenes (styrenes,6
2-vinylnaphthalene7) or vinylhetarenes8 has been developed (Scheme 1).
Scheme 1
At the same time, the literature lacks data on phosphorylation of allylarenes with
elemental phosphorus, though it is known that allylbromide reacts with red phosphorus
in the system KОН-Н2О-dioxane to give a mixture of tri(propen-2-yl)- and tri(propen-1-
yl)phosphane oxides.9
In this article, we report for the first time on the reaction of red phosphorus with
allylbenzene in superbasic system KOH-DMSO.
RESULTS AND DISCUSSION
We found that heating (130 оС, 3 h, argon blanket) red phosphorus and allylbenzene in
the KOH-DMSO suspension (including ∼ 0.1 mass% of hydroquinone as a radical processes
inhibitor) afforded a mixture of bis(1-methyl-2-phenylethyl)phosphane (1), bis(1-methyl-2-
phenylethyl)phosphane oxide (2), and potassium salt of 1-methyl-2-phenylethylphosphinic
acid in a ratio 2:1:3 (31P NMR). Free 1-methyl-2-phenylethylphosphinic acid (3) was
isolated from the acidified aqueous layer in 32% yield (Scheme 2).
The reaction mixture obtained was diluted with water and extracted with chloroform.
After removal of chloroform, a mixture of secondary phosphane 1 and phosphane oxide 2
was exposed in air (24 h, r.t.) to give secondary phosphane oxide 2 in 35% yield.
Microwave-assisted reaction of red phosphorus with allylbenzene not only shortened
the process duration, but it affected noticeably its chemoselectivity. So, a microwave irradi-
ation (200 W, 30 min) promoted version of the reaction (with the same reactants ratio) gave
mainly secondary phosphane 1 in 48% yield. In addition, the reaction delivered phosphinic
acid 3 (after acidic treatment) in 9% yield (Scheme 3).
In the absence of KOH, no reaction occurred. This fact confirms the nucleophilic
mechanism of the addition, which can be presented as follows (Scheme 4): In the first

1690
S. F. MALYSHEVA ET AL.
Scheme 2
Scheme 3
Scheme 4
stage, due to the [1,3H] isomerization of allylbenzene under the action of the superbase,
1-phenylprop-1-ene (A) is formed. The latter reacts with phosphorus-centered nucleophiles
generated by cleavage of the P–P bond in the presence of hydroxide anions. Nucleophilic
addition of phosphide- and phosphinite anions to the double bond of A results in phosphane
1 and phosphane oxide 2 (or acid salt 3), respectively.
The isolation of intermediate Е-1-phenylprop-1-ene (A) from the reaction mixture
supports the above mechanism.
According to the NMR data (1H, 13C, and 31P), secondary phosphane 1 and phosphane
oxide 2 have been formed as a mixture of diastereomers. So, in the 31P NMR spectra of
1
phosphine 1, three signals at –28.3, –22.8, and –17.4 ppm, in a ratio of 1:4:1 (d, JPH
207.3, 180.4, and 199.2 Hz); in the 31P NMR spectra of phosphine oxide 2, three signals
1
at 53.7, 49.7, and 47.3 ppm, in a ratio of 1:3:1 (d, JPH 438.7, 439.5, and 434.0 Hz) are

REACTION OF RED PHOSPHORUS WITH ALLYLBENZENE
1691
observed. The most intense signal (–22.8 and 49.7 for 1 and 2, respectively) corresponds
to the resonance of the major diastereomer where the configuration of the chiral carbon
atoms is identical (S,S or R,R). The second pair of diastereomers (RS, SR), in which the
configuration of the chiral carbon in the substituents is different, is presented by two weak
signals at –17.4 and –28.3 (for 1), and at 53.7 and 49.7 (for 2). The NMR spectra of minor
and major diastereomers of secondary phosphane 1 and phosphane oxide 2 are given in the
Experimental section.
It is worth noting that secondary phosphane 1 did not react with elemental sulfur or
selenium, though its structural congener, bis(2-phenylpropyl)phosphane, under the same
conditions readily formed secondary phosphane chalcogenides.10 The inactivity of sec-
ondary phosphane 1 is likely due to the presence of sterically hindered secondary alkyl
groups at the phosphorus atom.
In summary, the reaction of red phosphorus with allylbenzene in the system KOH-
DMSO has been accomplished for the first time. When applied to other allylarenes, this
reaction represents a simple and efficient pathway to novel chiral secondary phosphanes,
phosphane oxides, and phosphinic acids with sterically hindered moieties, possible ligands
for metal complex catalysts,11 and reactive building blocks for the synthesis of important
tertiary phosphines and corresponding phosphine chalcogenides,12 as well as intermediates
and coordinating solvents for the preparation of conductive nanomaterials.13
EXPERIMENTAL
IR spectra were measured with a Bruker IFS 25 instrument in microlayer or KBr
(cm−1). 1H, 13C, and 31P NMR spectra were recorded on a Bruker DPX-400 spectrometer
(400.13, 100.61, and 161.98 MHz, respectively) in C6D6 solution and referenced to internal
HMDS (1H), C6D6 (13C), and external 85% H3PO4 (31P). 2D homo- and heteronuclear NMR
1
correlation experiments (NOESY, HSQC) were used to assign the signals in Н and 13С
NMR spectra. Microwave mirradiation was performed in a Microwave oven, Samsung
M181DNR (max power level 850 W) equipped with reflux condenser. The brand KSAN
“SIA” red phosphorus was employed. Brand DMSO (1% water content) was used. All
reactions were conducted under argon atmosphere.
Synthesis of Secondary Phosphane Oxide 2 and Phosphinic Acid 3
A mixture of red phosphorus (3.10 g, 100 mmol), allylbenzene (4.71 g, 40 mmol),
KOH·0.5H2O (7.00 g, 108 mmol), DMSO (30 mL), and hydroquinone (0.14 g) was stirred
for 2 h at 130◦С, cooled, and analyzed by 31P NMR. The mixture contained secondary
phosphanes 1, phosphane oxide 2, and potassium salt of 1-methyl-2-phenylethylphosphinic
acid (3) in a 2:1:3 ratio, respectively. The mixture was diluted with water (30 mL) and
extracted with CHCl3 (3 × 20 mL). The chloroform extract was washed with a 20%
aq solution of KCl (3 × 15 mL) and dried over K2CO3. The solvent was removed under
reduced pressure. The residue was analyzed by 31Р NMR. The mixture contained secondary
phosphanes 1 and phosphane oxide 2 in a 2:1 ratio. The mixture was exposed to air for
24 h, washed with hexane, and dried in vacuo to give phosphane oxide 2. The aqueous
layer of the reaction mixture was acidified with a 35% aq НСl up to рН 4–5 and extracted
with chloroform (3 × 20 mL). The chloroform extract was washed with water (3 × 15 mL)

1692
S. F. MALYSHEVA ET AL.
and dried over CaCl2. The solvent was removed, and the residue was reprecipitated from
chloroform with hexane and dried in vacuo to give phosphinic acid 3.
Bis(1-methyl-2-phenylethyl)phosphane Oxide (2). Colorless viscous oil,
2.00 g (35%) yield. Major diastereomer: 1H NMR, δ (ppm), J (Hz): 0.91 (dd, 6H, 3JНН
=
3
7.1, JРН = 15.4, Me), 1.65 (m, 2H, CHMe), 2.44–3.06 (m, 1Н, CH2Ph), 2.44–2.80 (m,
1Н, CH2Ph), 6.11 (ddd, 1H, 1JPН = 439.5, 3JHН = 4.7 and 1.5, РН), 6.89–7.16 (m, 10H,
1
Ph). 13C NMR, δ (ppm), J (Hz): 12.4 (Me), 32.8 (d, JPC = 62.6, СНP), 35.5 and 37.2
(СН2Ph), 128.8 and 128.7 (C-o, C-m, Ph), 126.7 (C-p, Ph), 139.3 (d, 3JPC = 11.8, C-i, Ph).
31P NMR, δ (ppm): 49.7 (d, 1JPH = 439.5 Hz). Minor diastereomer 1: 1H NMR, δ (ppm), J
3
3
(Hz): 0.56 (dd, 6H, JНН = 7.2, JРН = 19.0, Me), 1.80 (m, 2H, CHMe), 2.30–3.16 (m,
1
3
2Н, CH2Ph), 6.08 (dt, 1H, JPН = 436.7, JHН = 3.6, РН), 6.89-7.16 (m, 10H, Ph). 13C
NMR, δ (ppm), J (Hz): 12.0 (Me), 32.2 (d, 1JPC = 63.4, СНP), 35.7 (СН2Ph), 129.6 and
129.6 (C-o, C-m, Ph), 126.3 (C-p, Ph), 139.3 (d, 3JPC = 10.7, C-i, Ph). 31P NMR, δ (ppm):
47.3 (d, 1JPH = 434.0 Hz). Minor diastereomer 2: 1H NMR, δ (ppm), J (Hz): 0.71 (dd, 6H,
3JНН = 7.1, 3JРН = 18.6, Me), 1.68 (m, 2H, CHMe), 2.30-2.70 (m, 2Н, CH2Ph), 6.16 (dt,
1H, 1JPН = 440.5, 3JHН = 2.6, РН), 6.89-7.16 (m, 10H, Ph). 13C NMR, δ (ppm), J (Hz):
1
13.2 (Me), 32.6 (d, JPC = 63.4, СНP), 36.9 (СН2Ph), 129.3 and 129.4 (C-o, C-m, Ph),
126.3 (C-p, Ph), 139.0 (d, 3JPC = 10.7, C-i, Ph). 31P NMR, δ (ppm): 53.7 (d, 1JPH = 438.7
Hz). IR ν (cm−1): 3374, 3293, 3107, 3085, 3062, 3027, 3002, 2966, 2929, 2874, 2853,
1603, 1495, 1454, 1379, 1242, 1198, 1155, 956, 913, 862, 753, 728, 700, 600, 586, 507,
481. Anal. Calcd. for C18H23ОP: С, 75.50; H, 8.10; P, 10.82. Found: С, 75.34; H, 8.15; P,
10.74.
1-Methyl-2-phenylethylphosphinic acid (3). Colorless viscous oil, 2.35 g
(32%) yield. 1H NMR, δ (ppm), J (Hz): 0.93 and 0.95 (dd, 3H, 3JНН = 7.1, 3JРН = 19.2,
Me), 1.87–1.95 (m, 1H, CHP), 2.34–2.43 (m, 1H, CH2Ph), 3.06–3.14 (m, 1H, CH2Ph),
6.90 (d, 1H, 1JPН = 535.0, РН), 6.92-7.08 (m, 5H, Ph), 13.56 (br. s, 1H, ОН). 13C NMR,
δ (ppm), J (Hz): 10.9 (Me), 34.9 (СН2Ph), 35.0 (d, 1JPC = 95.6, СНP), 126.6 (C-p, Ph),
128.7 (C-o, Ph), 129.4 (C-m, Ph), 139.0 (d, 3JPC = 14.1, C-i, Ph). 31P NMR, δ (ppm): 40.0
(1JPH = 535.0 Hz). IR ν (cm−1): 3620, 3086, 3062, 3028, 2968, 2933, 2876, 2632, 2374,
2356, 2343, 1667, 1603, 1496, 1455, 1380, 1243, 1202, 1175, 1080, 1058, 1028, 968, 903,
862, 820, 756, 729, 710, 700, 668, 657, 641, 621, 595, 584, 571, 521, 472. Anal. Calcd. for
C9H13О2P: С, 58.69; H, 7.11; P, 16.82. Found: С, 58.49; H, 7.18; 16.71.
Synthesis of Secondary Phosphane 1
A mixture of red phosphorus (3.10 g, 100 mmol), allylbenzene (9.00 g, 76 mmol),
hydroquinone (0.20 g), KОН·0.5H2O (7.00 g, 108 mmol), and DMSO (30 mL) was irradi-
ated in a microwave oven (200 W) for 30 min. The reaction mixture was cooled and diluted
with water (30 mL) and extracted with chloroform (3 × 30 mL). The extract was washed
with water (3 × 30 mL) and dried over K2CO3. Chloroform was distilled, and the residue
was fractionized in vacuo to give E-1-phenylprop-1-ene and secondary phosphane 1.
Bis(1-methyl-2-phenylethyl)phosphane (1). Colorless oil, bp 169–170◦C (1
1
Torr), 4.95 g (48%) yield. Major diastereomer: H NMR, δ (ppm), J (Hz): 1.03 (dd, 6H,
3
2
3JHH = 7.0, JPH = 13.2, Me), 2.07 (m, 2Н, CH), 2.51 and 2.85 (ddd, 4H, JHH = 10.0,
3
3
3
3JPH = 9.9, JPH = 8.0, JHH = 10.0, JHH = 5.9, CH2Ph), 2.78–2.87 (m, 2H, CH2Ph),
3.03 (dm, 1H, PH), 7.10–7.26 (m, 10H, Ph). 13C NMR, δ (ppm), J (Hz): 19.3 (d, JPC
2
= 15.8, Me), 27.3 (d, 1JPC = 10.6, СН), 42.8 (d, JPC 13.9, CH2Ph), 126.0 (C-p, Ph),
2
128.2 and 129.0 (C-o,m, Ph), 140.7 (d, 3JPC = 8.1, C-i, Ph). 31P NMR, δ (ppm): −22.8 (d,

REACTION OF RED PHOSPHORUS WITH ALLYLBENZENE
1693
1JPH = 180.4 Hz). Minor diastereomer: 1H NMR, δ (ppm), J (Hz): 1.06 (dd, 6H, 3JHH
=
=
3
2
7.0, JPH = 13.2, Me), 2.07, 2,47 and 2.81 (ddd, three-spin system ABM, 3H,, JAB
3
3
3
3
10.0, JPHA = 8.0, JPHB = 9.8 JAM = 5.9, JBM = 10.0, CH and CH2), 3.03 (dm, 1H,
PH), 7.10-7.26 (m, 10H, Ph). 13C NMR, δ (ppm), J (Hz): 19.2 (d, 2JPC = 16.5, Me), 27.3
(d, 1JPC = 10.6, СН), 42.6 (d, 2JPC = 13.2, CH2), 126.0 (C-p, Ph), 128.2 and 129.0 (C-o,m,
Ph), 140.6 (d, 3JPC = 7.3, C-i, Ph). 31P NMR, δ (ppm): −28.3 and −17.4 ppm (d, 1JPH
=
207.3 and 199.2 Hz). IR ν (cm−1): 3080, 3060, 3024, 2968, 2917, 2865, 2850, 2294, 1601,
1598, 1491, 1455, 1304, 1276, 1040, 1040, 968, 914, 736, 695. Anal. Calc. for C18H23P:
С, 79.97; H, 8.58; P, 11.46. Found: С, 79.83; H, 8.44; P, 11.21.
E-1-Phenylprop-1-ene. Colorless liquid, bp 35–40◦C (1 Torr), 1.10 g (12%) yield.
3
3
3
1H NMR (CDCl3) δ: 2.03 (d, 3H, JНH = 6.1, Me), 6.37 (dd, 1H, JНH = 15.4, JНH
=
3
6.1, = CHMe), 6.58 (d, 1H, JHH = 15.4, = CHPh), 7.28–7.43 (m, 5H, Ph). Anal. Calc.
for C9H10: С, 91.47; H, 8.53. Found: С, 91.40; H, 8.41.
REFERENCES
1. (a) Trofimov, B. A.; Gusarova, N. K.; Brandsma, L. Main Group Chem. News 1996, 4, 18–24;
(b) Gusarova, N. K.; Malysheva, S. F.; Arbuzova, S. N.; Trofimov, B. A. Russ. Chem. Bull. 1998,
47, 1645–1702; (c) Trofimov, B. A.; Gusarova, N. K. Mendeleev Commun. 2009, 19, 295–302.
2. Rauhut, M. M.; Bernheimer, R.; Semsel, A. M. J. Org. Chem. 1963, 28, 478–481.
3. Bogolyubov, G. M.; Petrov, A. A. Dokl. Akad. Nauk SSSR 1967, 173, 1076–1079 (in Russian).
4. Bornancini, E. R.; Alonso, R. A.; Rossi, R. A. J. Organomet. Chem. 1984, 270, 177–183.
5. Trofimov, B. A.; Gusarova, N. K.; Malysheva, S. F.; Vyalykh, E. P.; Rakhmatulina, T. N.;
Voronkov, M. G. Bull. Acad. Sci., Div. Chem. Sci. 1988, 37, 1284.
6. (a) Trofimov, B. A.; Gusarova, N. K.; Malysheva, S. F.; Rakhmatulina, T. N.; Voronkov, M. G.;
Dmitriev, V. I.; Shaikhudinova, S. I. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 55, 271–274;
(b) Trofimov, B. A.; Malysheva, S. F.; Gusarova, N. K.; Kuimov, V. A.; Belogorlova, N. A.;
Sukhov, B. G. Tetrahedron Lett. 2008, 49, 3480–3483.
7. (a) Gusarova, N. K.; Shaikhudinova, S. I.; Kazantseva, T. I.; Malysheva, S. F.; Sukhov, B. G.;
Belogorlova, N. A.; Dmitriev, V. I.; Trofimov, B. A. Russ. J. Gen. Chem. 2002, 72, 371–375;
(b) Gusarova, N. K.; Shaikhudinova, S. I.; Sukhov, B. G.; Kazantseva, T. I.; Malysheva, S. F.;
Smetannikov, Yu. V.; Tarasova, N. P.; Kuimov, V. A.; Trofimov, B. A. Russ. Chem. Bull. 2003,
52, 511–512.
8. (a) Trofimov, B. A.; Shaikhudinova, S. I.; Dmitriev, V. I.; Nepomnyashchikh, K. V.; Kazantseva,
T. I.; Gusarova, N. K. Russ. J. Gen. Chem. 2000, 70, 40–45; (b) Gusarova, N. K.; Shaikhudinova,
S. I.; Kazantseva, T. I.; Sukhov, B. G.; Dmitriev, V. I.; Sinegovskaya, L. M.; Smetannikov, Yu.
V.; Tarasova, N. P.; Trofimov, B. A. Chem. Heterocycl. Compd. 2001, 37, 576–580.
9. Malysheva, S. F.; Sukhov, B. G.; Gusarova, N. K.; Afonin, A. V.; Shaikhudinova, S. I.;
Kazantseva, T. I.; Belogorlova, N. A.; Kuimov, V. A., Plotnikova, G. V.; Trofimov, B. A. Russ.
J. Gen. Chem. 2004, 74, 1091–1095.
10. Malysheva, S. F.; Artem’ev, A. V.; Gusarova, N. K.; Timokhin, B. V.; Tatarinova, A. A.; Trofimov,
B. A. Russ. J. Gen. Chem. 2009, 79, 1259–1263.
11. (a) Pillarsetty, N.; Raghuraman, K.; Barnes, C. L.; Katti, K. V. J. Am. Chem. Soc. 2005, 127,
331–336; (b) Kovacik, I.; Scriban, C.; Glueck, D. S. Organometallics 2006, 25, 536–539;
(c) Scriban, C.; Glueck, D. S. J. Am. Chem. Soc. 2006, 128, 2788–2789; (d) Kakeya, M.;
Tanabe, M.; Nakamura, Y.; Osakada, K. J. Organomet. Chem. 2009, 694, 2270–2278.
12. (a) Delacroix, O.; Gaumont, A. C. Curr. Org. Chem. 2005, 9, 1851–1882; (b) Honaker, M. T.;
Hovland, J. M.; Salvatore, R. N. Curr. Org. Synth. 2007, 4, 31–45.
13. (a) Stefanescu, D. M.; Glueck, D. S.; Siegel, R.; Wasylishen, R. E. Langmuir 2004, 20,
10379–10381; (b) Stefanescu, D. M.; Glueck, D. S.; Siegel, R.; Wasylishen, R. E. J. Clust.
Sci. 2008, 19, 445–458.